Toluene → 5-Chlorocarbonylphthalide

HRID 1937068Notes

Reaction equation

HRID 1937068 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:9](=[O:10])[O:8][CH2:7]2)(O)=[O:2].C1(C)C=CC=CC=1.S(Cl)([Cl:23])=O.CN(C)C=O>CCCCCCC>[Cl:23][C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:9](=[O:10])[O:8][CH2:7]2)=[O:2]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 785171,3-Dihydro-1-oxoisobenzofuran-5-carboxylic acid

Product 1

HCID 98155555-Chlorocarbonylphthalide

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

5-Carboxyphthalid (53 g, 0.3 mole) was suspended toluene (200 mL) and thionylchloride (44 g, 0.6 mole). N,N-dimethylformamide (DMF) (1 mL) was added and the mixture was heated at reflux temperature for 3 hours. The mixture was cooled to room temperature and n-heptane was added (200 ml). The crystals formed were collected and washed with heptane (100 mL). Yield 52 g, 88%. DSC onset: 131° C. 1H NMR (CDCl3, 500 MHz): 5.47 (2H, s), 8.06 (1H, d , J=7.5 Hz), 8.28(1H, d, J=7.5 Hz), 8.3(1H, s). 13C NMR (CDCl3, 125 MHz): 69.4, 125.1, 126.1, 131.1, 131.6, 137.8, 146.6, 167.4, 169.0.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 3 hours
  3. customThe crystals formed
  4. customwere collected
  5. washwashed with heptane (100 mL)
  6. custom131° C

Sources & evidence

ORD record
ord-1cec08ce802f4e529f3a8d2151a5738c
Source dataset
uspto-grants-2002_05
Patent number
US06392060B1

Reaction notes

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